Itaconic acid

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  • Identifiers

    CAS number
    97-65-4

    Molecular formula
    C5H6O4

    SMILES
    C=C(CC(=O)O)C(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sour 52.59%
    Odorless 47.85%
    Caramellic 47.62%
    Burnt 40.0%
    Winey 35.53%
    Sharp 33.71%
    Sweet 31.22%
    Buttery 30.68%
    Nutty 26.0%
    Pungent 24.94%

     

    Flavor
    Odorless 59.95%
    Nutty 44.29%
    Sour 38.51%
    Very mild 35.65%
    Musty 30.01%
    Caramellic 29.02%
    Mild 26.63%
    Yeast 23.25%
    Acidic 22.26%
    Phenolic 21.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    6.31 (neutral)

    Molecular weight
    130.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 162-164 °C WITH DECOMP, ALSO REPORTED AS 172 °C
    • 175 °C

    Boiling point

    • 268 °C, SUBLIMES

    Flash point

    • 166.98 ˚C est.

    Solubility expt.

    • 1 G DISSOLVES IN 12 ML WATER, 5 ML ALC; VERY SLIGHTLY SOL IN BENZENE, CHLOROFORM, CARBON DISULFIDE, PETROLEUM ETHER
    • SOL IN ACETONE
    • 76.8 mg/mL at 20 °C

  • Synonyms

    • Itaconic acid
    • 97-65-4
    • 2-Methylenesuccinic acid
    • 2-methylidenebutanedioic acid
    • METHYLENESUCCINIC ACID
    • Propylenedicarboxylic acid
    • Methylenebutanedioic acid
    • itaconate
    • Butanedioic acid, methylene-
    • 2-Propene-1,2-dicarboxylic acid
    • Succinic acid, methylene-
    • 2-methylenebutanedioic acid
    • DTXSID2026608
    • NSC-3357
    • Q4516562YH
    • DTXCID006608
    • CHEBI:30838
    • methylidenebutanedioate
    • RefChem:792464
    • hydron;2-methylidenebutanedioate
    • 202-599-6
    • MFCD00004260
    • butanedioic acid, 2-methylene-
    • 25119-64-6
    • AI3-16901
    • CHEMBL359159
    • NSC3357
    • CAS-97-65-4
    • HSDB 5308
    • NSC 3357
    • EINECS 202-599-6
    • Methylenesuccinate
    • UNII-Q4516562YH
    • ITN
    • Methylenebutanedioate
    • 2-Methylenesuccinate
    • Propylenedicarboxylate
    • 2-methylenebutanedioate
    • Itaconic acid (Standard)
    • Itaconic acid, >=99%
    • 2-Methylene-Succinic Acid
    • bmse000137
    • Probes1_000076
    • Probes2_000247
    • EC 202-599-6
    • 2-Methylenesuccinic acid #
    • ITACONIC ACID [MI]
    • NCIStruc1_001783
    • NCIStruc2_000502
    • 2-methylene-butanedioic acid
    • NCIOpen2_004822
    • SCHEMBL21523
    • 2-Propene-1,2-dicarboxylate
    • orb1302523
    • SCHEMBL27676809
    • HY-Y0520R
    • Itaconic acid, analytical standard
    • Succinic acid, methylene- (8CI)
    • BB_NC-02310
    • HY-Y0520
    • Tox21_201299
    • Tox21_303071
    • BBL011584
    • BDBM50036216
    • LMFA01170063
    • s3095
    • STL163322
    • AKOS000118895
    • 2-Hydroxy-3-Naphthoyl-2-Naphthylamine
    • EBC-151087
    • MSK70032-1000W
    • SB67306
    • Butanedioic acid,ethylidene-,(E)-(9ci)
    • NCGC00249019-01
    • NCGC00257141-01
    • NCGC00258851-01
    • AS-11816
    • CS-0015302
    • M0223
    • NS00007642
    • EN300-18045
    • Itaconic acid Solution in Water, 1000ug/mL
    • C00490
    • E80791
    • F094482
    • Q903311
    • Z57127539
    • F2191-0234
    • 2-METHYLENE,1,4-BUTANEDIOIC ACID (ITACONIC ACID)
    • 53EEC7A3-4846-4588-BBC9-CB8846377B96
    • InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9
    • 97-65-4

  • Applications

    Itaconic acid (CAS 97-65-4) is a versatile biobased monomer used to generate poly(itaconic acid) and copolymers for waterborne coatings and paints, where its carboxyl functionality supports thickening, rheology control, and adhesion. It serves as a building block for rheology modifiers and polymeric thickeners in cosmetics and personal care, helping achieve stable texture and viscosity. It is also employed as a functional co-monomer or crosslinking partner in specialty polymers for inks and coatings, improving film formation and mechanical properties. In household and industrial cleaning formulations, itaconic acid and its salts act as chelating and dispersing agents to bind metal ions and stabilize surfactant systems. Additionally, itaconic acid is used as a biobased intermediate in polymer synthesis for sustainable plastics and materials research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 273.31
    methanol 485.44
    isopropanol 199.49
    water 726.41
    ethyl acetate 17.35
    n-propanol 190.72
    acetone 124.78
    n-butanol 154.67
    acetonitrile 28.02
    DMF 804.96
    toluene 5.29
    isobutanol 105.73
    1,4-dioxane 141.92
    methyl acetate 36.42
    THF 270.46
    2-butanone 65.87
    n-pentanol 95.74
    sec-butanol 138.54
    n-hexane 5.87
    ethylene glycol 314.45
    NMP 167.97
    cyclohexane 1.86
    DMSO 532.6
    n-butyl acetate 13.71
    n-octanol 33.43
    chloroform 9.05
    n-propyl acetate 17.87
    acetic acid 53.57
    dichloromethane 16.48
    cyclohexanone 39.33
    propylene glycol 166.38
    isopropyl acetate 13.62
    DMAc 364.85
    2-ethoxyethanol 316.9
    isopentanol 106.47
    n-heptane 3.63
    ethyl formate 73.23
    1,2-dichloroethane 20.45
    n-hexanol 56.51
    2-methoxyethanol 541.88
    isobutyl acetate 6.5
    tetrachloromethane 6.56
    n-pentyl acetate 12.8
    transcutol 99.61
    n-heptanol 36.99
    ethylbenzene 7.59
    MIBK 31.26
    2-propoxyethanol 153.34
    tert-butanol 247.75
    MTBE 63.57
    2-butoxyethanol 89.82
    propionic acid 38.66
    o-xylene 8.62
    formic acid 235.87
    diethyl ether 50.36
    m-xylene 7.08
    p-xylene 7.42
    chlorobenzene 3.19
    dimethyl carbonate 35.51
    n-octane 2.22
    formamide 299.29
    cyclopentanone 79.56
    2-pentanone 52.65
    anisole 34.55
    cyclopentyl methyl ether 53.26
    gamma-butyrolactone 81.02
    1-methoxy-2-propanol 266.22
    pyridine 24.7
    3-pentanone 27.78
    furfural 77.58
    n-dodecane 1.81
    diethylene glycol 214.79
    diisopropyl ether 11.09
    tert-amyl alcohol 163.09
    acetylacetone 37.71
    n-hexadecane 1.84
    acetophenone 24.57
    methyl propionate 31.51
    isopentyl acetate 12.42
    trichloroethylene 16.1
    n-nonanol 29.39
    cyclohexanol 47.78
    benzyl alcohol 43.96
    2-ethylhexanol 22.71
    isooctanol 24.63
    dipropyl ether 22.81
    1,2-dichlorobenzene 4.31
    ethyl lactate 27.18
    propylene carbonate 25.89
    n-methylformamide 332.62
    2-pentanol 76.89
    n-pentane 5.24
    1-propoxy-2-propanol 72.68
    1-methoxy-2-propyl acetate 21.85
    2-(2-methoxypropoxy) propanol 60.15
    mesitylene 6.18
    ε-caprolactone 34.27
    p-cymene 5.11
    epichlorohydrin 106.17
    1,1,1-trichloroethane 8.54
    2-aminoethanol 331.28
    morpholine-4-carbaldehyde 217.54
    sulfolane 113.91
    2,2,4-trimethylpentane 2.32
    2-methyltetrahydrofuran 98.61
    n-hexyl acetate 19.11
    isooctane 1.95
    2-(2-butoxyethoxy)ethanol 83.74
    sec-butyl acetate 9.99
    tert-butyl acetate 22.67
    decalin 1.99
    glycerin 242.52
    diglyme 145.61
    acrylic acid 35.65
    isopropyl myristate 9.37
    n-butyric acid 41.88
    acetyl acetate 7.28
    di(2-ethylhexyl) phthalate 11.53
    ethyl propionate 18.31
    nitromethane 92.29
    1,2-diethoxyethane 29.55
    benzonitrile 11.82
    trioctyl phosphate 12.21
    1-bromopropane 11.92
    gamma-valerolactone 120.85
    n-decanol 22.8
    triethyl phosphate 11.37
    4-methyl-2-pentanol 38.82
    propionitrile 29.64
    vinylene carbonate 22.53
    1,1,2-trichlorotrifluoroethane 82.21
    DMS 10.14
    cumene 7.05
    2-octanol 22.54
    2-hexanone 32.36
    octyl acetate 14.07
    limonene 6.55
    1,2-dimethoxyethane 379.9
    ethyl orthosilicate 11.68
    tributyl phosphate 10.09
    diacetone alcohol 73.82
    N,N-dimethylaniline 38.23
    acrylonitrile 35.2
    aniline 18.01
    1,3-propanediol 303.55
    bromobenzene 2.15
    dibromomethane 9.78
    1,1,2,2-tetrachloroethane 19.01
    2-methyl-cyclohexyl acetate 11.28
    tetrabutyl urea 22.48
    diisobutyl methanol 14.65
    2-phenylethanol 30.75
    styrene 6.74
    dioctyl adipate 12.65
    dimethyl sulfate 68.85
    ethyl butyrate 13.85
    methyl lactate 55.85
    butyl lactate 18.3
    diethyl carbonate 8.96
    propanediol butyl ether 69.95
    triethyl orthoformate 12.85
    p-tert-butyltoluene 5.59
    methyl 4-tert-butylbenzoate 31.09
    morpholine 199.84
    tert-butylamine 98.45
    n-dodecanol 17.25
    dimethoxymethane 331.64
    ethylene carbonate 20.57
    cyrene 63.97
    2-ethoxyethyl acetate 17.37
    2-ethylhexyl acetate 8.06
    1,2,4-trichlorobenzene 4.98
    4-methylpyridine 31.07
    dibutyl ether 16.18
    2,6-dimethyl-4-heptanol 14.65
    DEF 99.9
    dimethyl isosorbide 67.35
    tetrachloroethylene 17.19
    eugenol 43.99
    triacetin 12.99
    span 80 35.7
    1,4-butanediol 169.2
    1,1-dichloroethane 11.78
    2-methyl-1-pentanol 65.32
    methyl formate 227.44
    2-methyl-1-butanol 100.86
    n-decane 2.82
    butyronitrile 35.52
    3,7-dimethyl-1-octanol 21.95
    1-chlorooctane 8.19
    1-chlorotetradecane 3.76
    n-nonane 2.75
    undecane 2.21
    tert-butylcyclohexane 2.38
    cyclooctane 1.33
    cyclopentanol 83.43
    tetrahydropyran 61.92
    tert-amyl methyl ether 52.76
    2,5,8-trioxanonane 106.02
    1-hexene 14.26
    2-isopropoxyethanol 130.13
    2,2,2-trifluoroethanol 54.95
    methyl butyrate 32.21

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction